Acetic Anhydride → HCID 131730828, compound

HRID 2176903Notes

Reaction equation

HRID 2176903 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]1>N1C=CC=CC=1>[C:1]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67070431HCID 67070431, compound

Product 1

HCID 131730828HCID 131730828, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (1.20 ml, 12.7 mmol) was added to a solution of trans-methyl 3-aminocyclohexane-carboxylate (0.40 g, 2.54 mmol) in pyridine (10 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for 1 h. The volatiles were removed in vacuum, the resulting residue was dissolved in DCM and washed with saturated sodium bicarbonate solution followed by brine solution (10 ml). After drying over anhydrous sodium sulfate and filtration the filtrate was concentrated under vacuum to afford 350 mg (69.0%) of trans-methyl 3-acetamidocyclohexanecarboxylate as a colorless liquid.

Workup

  1. customThe volatiles were removed in vacuum
  2. dissolutionthe resulting residue was dissolved in DCM
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialAfter drying over anhydrous sodium sulfate and filtration the filtrate
  5. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-7a0fc787bc5b405f87f3a13c52d1638a
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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